Charge delocalization and enhanced acidity in tricationic superelectrophiles

Rajasekhar Reddy Naredla, Chong Zheng, Sten O. Nilsson Lill, Douglas A. Klumpp

Research output: Contribution to journalArticlepeer-review

36 Scopus citations

Abstract

This Article presents the results from studies related to the chemistry of tricationic superelectrophiles. A series of triaryl methanols were ionized in Brønsted superacids, and the corresponding tricationic intermediates were formed. The trications are found to participate in two types of reactions; both are characteristic of highly charged organic cations. One set of reactions occurs through charge migration. A second set of reactions occurs through deprotonation of an unusually acidic site on the tricationic species. One of the tricationic intermediates has been directly observed by low temperature NMR spectroscopy. These highly charged ions and their reactions have also been studied using density functional theory calculations. As a result of charge migration, electron density at a carbocation site is found to increase with progression from monocationic to pentacationic structures.

Original languageEnglish (US)
Pages (from-to)13169-13175
Number of pages7
JournalJournal of the American Chemical Society
Volume133
Issue number33
DOIs
StatePublished - Aug 24 2011

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